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Stereoselective trimethylsilylation of α- and β-galactopyranoses

Author:
Asami, Yuri, Kawaguchi, Yuka, Kanie, Yoshimi, Abdu-Allah, Hajjaj, Suzuki, Katsuhiko, Kanie, Osamu
Source:
Carbohydrate research 2019 v.474 pp. 51-56
ISSN:
0008-6215
Subject:
galactosides, gel chromatography, moieties, stereoselectivity
Abstract:
Trimethylsilylation of the anomeric hydroxyl groups of tetra-O-benzyl and tetra-O-acetyl galactopyranoses was investigated. Stereoselective formation of β-trimethylsilyl glycoside (β-TMS glycoside) of benzyl protected compound was achieved using N-trimethylsilyl diethylamine. In the course of the investigation of the selective synthesis of TMS galactosides using TMS-imidazole, we observed the formation of an intermediate, which was converted predominantly into α-TMS glycoside after silica gel column chromatography. A reaction of acetylated compound using TMS-trifluoromethanesulfonate–2,6-lutindine selectively yielded α-TMS glycoside.
Agid:
6297057